An efficient methodological approach for synthesis of selenopyridines: generation, reactions, anticancer activity, EGFR inhibitory activity and molecular docking studies.

In the present work, we successfully synthesized Se-alkyl selenopyridines 1 and 3, selenopheno[2,3-b]pyridine 2, and bis-selenopyridine 4 derivatives using an eco-friendly method by utilizing NaHSe instead of toxic hydrogen selenide. The effect of the temperature on the reaction was screening at various temperatures. The regiospecific reaction of selenopyridine 1 with bromine afforded an unexpected product 4,6-diamino-5-bromo-2-[(cyanomethyl)selenyl]-pyridine-3-carbonitrile (5), which was cyclized to selenopheno[2,3-b]pyridine (7) by refluxing in the presence of TEA. While its treatment with thiophenol and/or p-chlorothiophenol gave 8a, b. On the other hand, its reaction with aminothiophenol afforded 2-(benzo[d]-thiazol-2-yl)-5-bromoselenopheno[2,3-b]pyridine-3,4,6-triamine (9). Also, N-(2-cyano-4-methyl-5H-1-seleno-3,5,8-triazaacenaphthylen-7-yl)acetamide (11) and a novel series of selenoazo dyes 12a-d were synthesized by treatment of selenopheno[2,3-b]pyridine 2 with acetic anhydride and/or diazonium chlorides of aromatic amines, respectively. Then, we ascertained the potential activity of synthesized compounds against highly metastatic prostate cancer cells (PC-3) and osteosarcoma cells (MG-63) and found that 12a, 12b, 12c, and 12d were more cytotoxic than doxorubicin in both tested cell lines, showing nearly the same anticancer activity with IC50 values ranging from 2.59 ± 0.02 µM to 3.93 ± 0.23 µM. Mechanistically, the most potent compounds 12a and 12b proved to be potent EGFR inhibitors with IC50 values of 0.301 and 0.123 µM, respectively, compared to lapatinib as a positive reference (IC50 = 0.049 µM). Moreover, the docking results are in good agreement with the anticancer activity as well as the EGFR inhibitory activity, suggesting these two compounds as promising EGFR anticancer candidates.

Synthesis and Insecticidal Evaluation of 3,5-Dicyanopyridines Against Cotton Aphids via Microwave-Assisted Multicomponent Reactions.

Certain 2-amino-6-alkoxy-4-arylpyridine-3,5-dicyanide 1a-e were prepared via a straightforward process using microwave technology rather than conventional methods. This involved reaction of arylidenemalononitrile thru propanedinitrile in the occurrence of sodium alkoxide under MW. While, their positional isomer 4-amino-6-alkoxy-2-arylpyridine-3,5-dicyanide 3a-j have been separated from the reaction of aryl aldehydes with 2-aminoprop-1-ene-1,1,3-tricarbonitrile 2 in the presence of sodium alkoxide using microwave technic. Furthermore, the insecticidal properties of all synthesized compounds were observed with respect to Cotton aphid nymphs and adults. Neonicotinoid pesticides are indicated as the most effective pesticides toward aphids and many other pests. Many insecticides are discovered as novelties. As a result, several pyridine compounds were chemical method synthesized to serve as equivalents of neonicotinoids, a broad class of insecticides. With LC50 value of 0.03 mg/L, components 3g exhibit the highest insecticidal bioactivity. This work discusses how to find new chemicals that could be used as insecticidal agents in the future.

Designing, Characterization, DFT, Biological Effectiveness, and Molecular Docking Analysis of Novel Fe(III), Co(II), and Cu(II) Complexes Based on 4-Hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione.

The main target of the current framework is the designing and synthesizing of novel iron(III), cobalt(II), and cupper(II) complex compounds emanating from bioactive nucleus, 4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione ligand, to enhance comprehension as potential antibacterial, antifungal, and antioxidant alternatives by means of using DFT calculations and molecular docking investigation. Thus, the new complexes had been synthesized and characterized using various analytical techniques, including elemental analysis, infrared spectroscopy, mass spectrometry, UV spectroscopy, conductivity, and magnetic testing, as well as thermal analysis. The 4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione ligand exhibits monobasic bidentate OO donor properties toward the metal core, as shown by its infrared spectroscopic characteristics. The use of thermal analysis techniques allows for the identification and characterization of water molecules present inside the complexes, as well as the determination of their distribution patterns. The molecular structures of free ligand and its metal complex compounds have been verified through the use of density functional theory (DFT) simulations. These simulations also provide a valuable understanding of the quantum chemical characteristics associated with these structures. In vitro experiments were conducted to evaluate the antioxidant, antibacterial, as well as antifungal and the properties of the free ligand and its corresponding complex compounds. DATA revealed that synthesized metal complex compounds have heightened biological efficacy as related to the unbound ligand. Furthermore, molecular docking analysis was done to understand the interactions between the studied compounds and proteins derived from Escherichia coli (pdb ID: 2vf5), Aspergillus flavus (pdb ID: 3cku), and humans (pdb ID: 5IJT), which are considered to be significant in drug design. Lastly, a correlation between in vitro efficacies with molecular docking data was done and analyzed.

Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin.

The optimized synthesis of [5-oxo-4,4-diphenylimidazolidin-2-ylidene]cyanamide, which is known as 2-cyanoguanidinophenytoin (CNG-DPH) (3), and (imidazo[4,5-d]imidazole-2,5-diylidine)dicyanamide (4) has been reported in the present work. Furthermore, new Mannich bases derived from CNG-DPH were synthesized via its reaction with formaldehyde and using the corresponding amines, piperidine (base 5), and morpholine (base 6). Also, the antimicrobial activity and X-ray crystal structures for CNG-DPH and their Mannich bases were studied. The bases 3 and 6 crystallized in a monoclinic system; the crystal structure of 3 containing four molecules in the unit cell with a P21/c space group. The unit cell of 6 has eight molecules with a C2/c space group. The inter and intra hydrogen bond contacts packed and stabilized both of the structures. The morpholine ring of base 6 demonstrated a distinctive chair configuration. Mannich bases 5 and 6 showed promising antimicrobial effects. base 4 has a greater percentage for in vitro cytotoxicity (IC50) against normal cells, whereas 3 has the lowest ratio.

Functionalized Pyridines: Synthesis and Toxicity Evaluation of Potential Insecticidal Agents against Aphis craccivora.

Using ultrasound technology instead of traditional methods, some pyridine derivatives were prepared by a simple procedure via a four-component reaction of different aromatic aldehydes, acetyl aryl, sodium alkoxide, and malononitrile, and additionally, all prepared compounds were monitored for insecticidal activities toward nymphs and adults of cowpea aphid. Though a lot of insecticides are discovered as a novelty on the other hand, neonicotinoid compounds are reflected as the most affected insecticides against aphids and many other pests. Thus, some of the pyridine derivatives were chemically prepared as analogues to a large group of insecticides called neonicotinoids. Under laboratory conditions, the toxicity of these components was measured toward adults and nymphs of Aphis craccivora. With respect to the LC50 values, components 1f, 1d, and 1c have the utmost insecticidal bioactivity, with values of 0.080, 0.098, and 0.127 mg/L. This work covers the way to discover novel compounds for the prospective use as insecticidal representatives.

Synthesis, Characterization, Antimicrobial, Density Functional Theory, and Molecular Docking Studies of Novel Mn(II), Fe(III), and Cr(III) Complexes Incorporating 4-(2-Hydroxyphenyl azo)-1-naphthol (Az).

This work synthesized three new CrAz2, MnAz2, and FeAz2 complexes and investigated them using IR, mass, UV spectroscopy, elemental analysis, conductivity and magnetic tests, and thermogravimetric analysis. The azo-ligand, 4-(2-hydroxyphenylAzo)-1-naphthol (Az), couples with metal ions via its nitrogen (in -N=N- bonds) and oxygen (in hydroxyl group) atoms, according to the IR spectra of these complexes. Through thermal examination (TG/TGA), the number and location of water in the complexes were also determined. Density functional theory (DFT) theory is applied to ameliorate the structures of the ligand (Az) and metal complexes and analyze the quantum chemical characteristics of these complexes. The antifungal and antibacterial activity of the ligand and its complexes opposed to several hazardous bacteria and fungi was investigated in vitro. Metal complexes were discovered to have a higher inhibitory impact on some organisms than the free ligand. The MnAz2 complex exhibited the best activity among the studied materials, whereas the CrAz2 complex had the lowest. The compounds' binding affinity to the E. coli (PDB ID: 1hnj) structure was predicted using molecular docking. Binding energies were calculated by analyzing protein-substrate interactions. These encouraging findings imply that these chemicals may have physiological effects and may be valuable for a variety of medical uses in the future.

Designing, characterization, biological, DFT, and molecular docking analysis for new FeAZD, NiAZD, and CuAZD complexes incorporating 1-(2-hydroxyphenylazo)- 2-naphthol (H2AZD).

Herien, three new Fe(III) (FeAZD), Ni(II) (NiAZD), and Cu(II) (CuAZD) complexes were synthesized and characterized using various physicochemical and spectroscopic approaches. The H2AZD ligand acted as a bi-basic bi-dentate NO ligand in a 1:1 molar ratio. The results revealed that the FeAZD and CuAZD complexes had octahedral geometry, while the NiAZD had a tetrahedral geometry. The optimized geometry, HOMO and LUMO analysis of the ligand and its metal complexes was determined via Density functional theory (DFT) using the B3LYP with 6-311 G(d,p), and LanL2DZ level of theory. The FeAZD, NiAZD and CuAZD had lower energy gap, 7.40, 7.93 and 7.06 eV, respectively, than the free ligand (9.58 eV), which proposed that CuAZD was more active one. The free ligand and its metal complexes were in vitro investigated for their antibacterial and antifungal activity. The results illustrated that the metal complexes had higher antibacterial and antifungal activity than the free ligand. More specifically, the CuAZD demonstrated good antibacterial activity against E. coli, P. aeruginosa, S. aureus, B. cereus, and A. flavus, T. rubrum, and C. albicans, with activity indexes of 72.22%, 65.01%, 77.78%, and 72.22%, 63.16%, 59.09%, and 61.90%, respectively. Also, the metal complexes showed lower MIC (6.25-3.125 ppm) compared to the free ligand (about 50 ppm). Finally, molecular docking was utilized to investigate the ability of the free ligand and its metal complexes to inhibit the growth of E. coli (PDB ID: 5iq9). The results showed that the CuAZD had the highest binding affinity to the receptor, with a more negative docking score of - 7.05 Kcal/mol, and lower inhibition constant (Ki) of 6.90 µM. That is indicating that it may be the most effective at inhibiting the growth of E. coli (PDB ID: 5iq9).

Construction of novel polybenzoxazine coating precursor exhibiting excellent anti-corrosion performance through monomer design.

In this study, we utilized salicylaldehyde (SA) and p-toluidine (Tol-NH2) to synthesize 2-(Z)[(4-methylphenyl)imino]methylphenol (SA-Tol-SF), which was then reduced to 2-[(4-methylphenyl)amino]methylphenol, producing SA-Tol-NH. SA-Tol-NH was further reacted with formaldehyde to create SA-Tol-BZ monomer. Poly(SA-Tol-BZ) was produced by thermally curing it at 210 °C, after synthesizing it from SA-Tol-BZ. The chemical structure of SA-Tol-BZ was analyzed using various analytical techniques such as FT-IR, 1H NMR spectroscopy, and 13C NMR spectroscopy TGA, SEM, DSC, and X-ray analyses. Afterward, we applied the obtained poly(SA-Tol-BZ) onto mild steel (MS) using thermal curing and spray coating techniques. To examine the anticorrosion attributes of MS coated with poly(SA-Tol-BZ), electrochemical characterization was employed. The study proved that poly(SA-Tol-BZ) coating had a high level of effectiveness in preventing corrosion on MS, with an efficacy of 96.52%, and also exhibited hydrophobic properties.

Synthesis, characterization and protective efficiency of novel polybenzoxazine precursor as an anticorrosive coating for mild steel.

In this study, 2-[(E)-(hexylimino)methyl] phenol (SA-Hex-SF) was synthesized by adding salicylaldehyde (SA) and n-hexylamine (Hex-NH2), which was subsequently reduced by sodium borohydride to produce 2-[(hexylamino)methyl] phenol (SA-Hex-NH). Finally, the SA-Hex-NH reacted with formaldehyde to give a benzoxazine monomer (SA-Hex-BZ). Then, the monomer was thermally polymerized at 210 °C to produce the poly(SA-Hex-BZ). The chemical composition of SA-Hex-BZ was examined using FT-IR, 1H, and 13C NMR spectroscopy. Differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and X-ray Diffraction (XRD), respectively, were used to examine the thermal behavior, surface morphology, and crystallinity of the SA-Hex-BZ and its PBZ polymer. Mild steel (MS) was coated by poly(SA-Hex-BZ) which was quickly prepared using spray coating and thermal curing techniques (MS). Finally, the electrochemical tests were used to evaluate the poly(SA-Hex-BZ)-coating on MS as anti-corrosion capabilities. According to this study, the poly(SA-Hex-BZ) coating was hydrophobic, and corrosion efficiency reached 91.7%.

Synthesis, DFT, Biological and Molecular Docking Analysis of Novel Manganese(II), Iron(III), Cobalt(II), Nickel(II), and Copper(II) Chelate Complexes Ligated by 1-(4-Nitrophenylazo)-2-naphthol.

Novelmanganese(II), iron(III), cobalt(II), nickel(II), and copper(II) chelates were synthesized and studied using elemental analysis (EA), infrared spectroscopy, mass spectrometry, ultraviolet-visible spectroscopy, and conductivity, as well as magnetic measurements and thermogravimetric analysis (TG). The azo-ligand 1-[(4-nitrophenyl)diazenyl]-2-naphthol (HL) chelates to the metal ions via the nitrogen and oxygen centers of the azo group and the hydroxyl, respectively. The amounts of H2O present and its precise position were identified by thermal analysis. Density functional theory (DFT) was employed to theoretically elucidate the molecular structures of the ligand and the metal complexes. Furthermore, the quantum chemical parameters were also evaluated. The antimicrobial properties were evaluated against a group of fungal and bacterial microbes. Interestingly, the bioactivity of the complexes is enhanced compared to free ligands. Within this context, the CuL complex manifested the lowest activity, whereas the FeL complex had the greatest. Molecular docking was used to foretell the drugs' binding affinity for the structure of Escherichia coli (PDB ID: 1hnj). Protein-substrate interactions were resolved, and binding energies were accordingly calculated.

Electrifying passenger road transport in India requires near-term electricity grid decarbonisation.

Battery-electric vehicles (BEV) have emerged as a favoured technology solution to mitigate transport greenhouse gas (GHG) emissions in many non-Annex 1 countries, including India. GHG mitigation potentials of electric 4-wheelers in India depend critically on when and where they are charged: 40% reduction in the north-eastern states and more than 15% increase in the eastern/western regions today, with higher overall GHGs emitted when charged overnight and in the summer. Self-charging gasoline-electric hybrids can lead to 33% GHG reductions, though they haven't been fully considered a mitigation option in India. Electric 2-wheelers can already enable a 20% reduction in GHG emissions given their small battery size and superior efficiency. India's electrification plan demands up to 125GWh of annual battery capacities by 2030, nearly 10% of projected worldwide productions. India requires a phased electrification with a near-term focus on 2-wheelers and a clear trajectory to phase-out coal-power for an organised mobility transition.

Eco-friendly and regiospecific intramolecular cyclization reactions of cyano and carbonyl groups in N,N-disubstituted cyanamide.

Eco-friendly, low-cost and high-yielding synthetic route toward imidazoles and oxazoles has been developed. 1-(4,6-Dimethylpyrimidin-2-yl)-2-(alkylamino)-1,5-dihydro-4H-imidazol-4-one 3a-c have been synthesized via regiospecific reaction of ethyl 2-(N-(4,6-dimethylpyrimidin-2-yl)cyanamide)acetate 1 with primary aliphatic amines in water as green solvent. While, the reaction between 4,6-dimethylpyrimidin-2-yl(2-oxo-2-phenylethyl)cyanamide 2 and primary aliphatic amines using water and/or iso-propanol as green solvents afforded 3-(4,6-dimethylpyrimidin-2-yl)-5-phenyl-1,3-oxazole-2(3H)-imine 6 and 1-(4,6-dimethylpyrimidin-2-yl)-N-alkyl-4-phenyl-1H-imidazol-2-amine 7a-d, respectively.

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors.

A novel series of ciprofloxacin hybrids comprising various heterocycle derivatives has been synthesized and structurally elucidated using 1H NMR, 13C NMR, and elementary analyses. Using ciprofloxacin as a reference, compounds 1-21 were screened in vitro against Gram-positive bacterial strains such as Staphylococcus aureus and Bacillus subtilis and Gram-negative strains such as Escherichia coli and Pseudomonas aeruginosa. As a result, many of the compounds examined had antibacterial activity equivalent to ciprofloxacin against test bacteria. Compounds 2-6, oxadiazole derivatives, were found to have antibacterial activity that was 88 to 120% that of ciprofloxacin against Gram-positive and Gram-negative bacteria. The findings showed that none of the compounds tested had antifungal activity against Aspergillus flavus, but did have poor activity against Candida albicans, ranging from 23% to 33% of fluconazole, with compound 3 being the most active (33% of fluconazole). The most potent compounds, 3, 4, 5, and 6, displayed an IC50 of 86, 42, 92, and 180 nM against E. coli DNA gyrase, respectively (novobiocin, IC50 = 170 nM). Compounds 4, 5, and 6 showed IC50 values (1.47, 6.80, and 8.92 µM, respectively) against E. coli topo IV in comparison to novobiocin (IC50 = 11 µM).